A Wind-Swept Surprise Proposal in Ocean Park, Puerto Rico

When the moment feels effortless, the memories last forever.

     Some proposals are meticulously planned down to the second. Others feel like a leap of faith—equal parts excitement, nerves, and love. Austin and Bailey’s surprise marriage proposal in Puerto Rico was both.

     I was brought on by I Do Proposal, an up-and-coming marriage proposal planning company here in Puerto Rico, to photograph a heartfelt surprise proposal along the shores of Ocean Park. Their client, Austin, had one goal in mind: ask his longtime girlfriend, Bailey, to spend forever with him—somewhere unforgettable.

From Georgia to Puerto Rico: A Shared Beginning

A quiet beach, a deep breath, and one life-changing question.

     The morning of the proposal, I reached out to Austin to go over final details. His phone number started with a 404 area code, one I know all too well. It turns out Austin and Bailey are from Georgia, a state where I once lived when I first moved to the U.S. That unexpected connection instantly broke the ice.

     Austin works in cybersecurity, Bailey at a hospital back home, and the two have been inseparable for nearly six years. Like many couples, their journey has been built on shared growth, stability, and genuine companionship—exactly the kind of foundation that makes proposal days so emotionally charged.

The Location: Yardley Street Beach Access, Condado

Wind in the air, love everywhere.

     While Ocean Park was the original vision, Katherinne, owner of I Do Proposal, selected Yardley Street in Condado for its discreet beach access and generous space. The entrance opens directly onto the sand, making it ideal for a private setup without feeling isolated—especially important for surprise proposals.

     That afternoon, the wind was relentless, which meant timing was everything. The decor—minimalist and intentional—consisted of a circle of red roses near the water, rose petals inside the circle, and a chilled bottle of champagne with flutes waiting nearby. We waited until the very last second to place the final petals to keep them from scattering across the beach.

A Perfectly Executed Proposal

She said yes, and the world stood still.

     Before the proposal, I gave Austin the usual rundown: where to stand, what to do, and—just as importantly—what not to do. No matter how many proposals I photograph (and I’ve shot over forty this year alone), the nerves never disappear. Asking someone to spend the rest of their life with you is a monumental moment.

As Austin and Bailey approached, everything fell into place.

     Austin gently positioned Bailey against the wind, an often-overlooked detail that makes a world of difference. Hair flying forward during the proposal moment can block reactions and emotions on camera—something I always coach proposers on. He even remembered to carefully tuck her hair behind her ear at just the right moment.

     Bailey’s reaction was pure, emotional, and completely unguarded. She didn’t see it coming at all.

After the “Yes”

Emotion over perfection—always.

     Once the initial wave of emotions settled and I knew I had the proposal documented exactly as it deserved, I stepped in to introduce myself—usually to a newly engaged partner who is either overwhelmed with emotion or still processing what just happened.

This time, it was both.

     Austin exhaled what felt like six years’ worth of anticipation, and we transitioned seamlessly into portraits. These two were a dream to photograph—affectionate, playful, and entirely wrapped up in each other. Their energy aligned perfectly with my approach to proposal photography: intimate, passionate, and real.

     As the sun dipped lower, I closed out the session with flash photography, adding a cinematic edge to an already unforgettable moment. When couples are this present with each other, they forget the camera exists—and that’s when the magic happens.

Why Puerto Rico Is the Perfect Place to Propose

A surprise proposal done right feels timeless.

     Ocean Park and Condado offer a rare combination of tropical beauty, accessibility, and privacy. Pair that with a thoughtful planner and intentional photography, and you’re left with something far more meaningful than a simple “yes.”

     Austin and Bailey’s proposal wasn’t just a question—it was a chapter. And I was honored to document it.

Capturing the moment they didn’t even know was happening.

🌈 A Love Reunited: Larry & Victor’s Sunrise Proposal in Puerto Rico

Love always finds its way back home — sometimes even after 17 years.

     Every so often, a story comes along that reminds me why I do what I do. Larry’s first email landed in my inbox like a beam of light — heartfelt, vulnerable, full of history and love that had clearly been waiting years to bloom again.

He wrote:

“I saw your website and fell in love... I’m going to propose to my boyfriend Victor… We actually dated 17 years ago… We parted as friends, reunited this year, and we are ready. It’s time.”

     From that moment, I knew this wasn’t just another surprise proposal in Puerto Rico. This was a full-circle moment, a love story touching down again right where it began — on the island that had once been their grand romantic gesture.

Reconnecting and Planning the Perfect Proposal

Two hearts, one sunrise, and a forever that finally arrived.

     Larry and I connected over FaceTime the moment he had a chance to sneak away. He joked that he set my notifications to silent so Victor wouldn’t suspect anything — borderline cheating, he laughed. That’s when I knew this proposal wasn’t just important… it was sacred.

     Originally, we planned to shoot at La Concha Resort, a venue where I’ve photographed countless weddings and engagements. But life happens, and that location fell through. Instead of stress, we pivoted — and honestly, the universe did us a favor.

     We set our sights east toward El Conquistador Resort in Fajardo, a stunning oceanfront property known for breathtaking sunrises. Why sunrise? Because Larry was drawn to the idea of a Blue Hour proposal — that magical sliver of time before the sun rises, when the world is quiet, the light is soft, and the moment belongs solely to the couple.

Blue Hour: A Challenge Worth Every Second

Because all love stories deserve to be celebrated in the light they were meant for.

     I woke up at 3:00 a.m., drove to Old San Juan to pick up my videographer, Bryan, and headed to Fajardo. By the time we arrived, the sky was still pitch black. We valeted the car, hopped onto the resort’s funicular, and started prepping gear we could barely see.

Blue Hour photography is rewarding — but it’s not for the faint of heart.
Your location is empty.
Your colors turn cinematic.
But… you’re also shooting in near darkness. As 6:00 a.m. approached, the faintest hint of orange teased the horizon. It was time.

The Moment Larry Dropped to One Knee

Love is love — and this moment was pure magic.

     Communication with Larry was spotty — understandably, since he couldn’t risk letting Victor see a single notification from me. Thankfully, the concierge team escorted them down to the green area we had planned for.

Bryan and I hid behind a gazebo, sneaking around like undercover agents every time they shifted direction.

When they reached the palm trees, morning light finally began revealing the world around us.

I had told Larry:
“Drop to one knee at 6:10 a.m. — not earlier.”
He did it at 6:15 a.m.

Still a touch dim… but the heart doesn’t care about ideal lighting. He felt the moment. He took it.

Victor turned toward him — shocked, emotional — and they slipped matching rings onto each other’s hands. I’d never seen matching proposal rings before. It was beautiful.

And then? A moment I’ll never forget:
Larry turned to Bryan and whispered, “Francis…?”

That’s how dark it still was. Even after FaceTime, he couldn’t tell us apart. We laughed for minutes.

The Engagement Session That Followed

Sunrise proposals and soul-deep connections — my favorite kind of morning.

     Once the sun broke fully over the horizon, we transitioned into their engagement shoot. Bryan focused on video, while I balanced between creative flash and the dreamy pastel light only sunrise can give you.

Their chemistry was effortless.
Their joy was contagious.
And their story — 17 years apart, now finding their way back to each other — felt powerful in every frame.

Why This Story Matters to Me

Here’s to the couples who choose love boldly, beautifully, and unapologetically.

     As a wedding and proposal photographer in Puerto Rico, I’ve documented over thirty surprise proposals just this year alone. But this one carried a weight beyond the photographs.

     As someone who proudly welcomes all couples — especially LGBTQIA+ couples — capturing Larry and Victor’s moment reminded me why visibility matters. Too many same-sex couples still hesitate when choosing a photographer. Too many wonder if they’ll be judged or treated differently.

My mission is simple:
Love is love, and every couple deserves a photographer who celebrates them wholeheartedly. To Larry and Victor — thank you for trusting me. For letting me witness your sunrise, your reunion, your beginning.

Wishing you both a beautiful life together. 🌈💍✨